Monoazo dyestuffs



Patented Sept. 22, 1936 un rno asm'res MoNoAzo DYESTI-IEFS Richard Fleischhauer, Frankfort-on-the-Maine Fechenheim,- Germany, ,assignor .to General Aniline Works, Inc., New

ration of Delaware No Drawing. Original application October 1,. f

l 33',"serial No; 692,700.. Divided. and this. ap-

plication April 30, 1935, Serial No. 19, 118.. In Germany October 13, 1932;

4 Claims. (01. 260-92) 7 The presentapplication' is a divisionof my at: plicat-ionSerial No; 692,790; filed ()ctober '7', 1933, and relating to monoazodyestufis. f

My present invention relates to monoazodyestuffs more particularly to those corresponding to the general formula: I r

i i N o-phenyl v 7 wherein R and Y have the aforesaid signification.

In order to further illustrate my invention the following examples are given; but I wish it, however, to be understood-that my invention is not limited to the particular products or reaction condition stated therein.

Example 1 18.5 parts of Z-amino-diphenylether are diazotized in the usual manner. The obtained diazosolution is allowed to run while cooling into a solution of 28.5 parts of 2-acetylamino-8-naphthol-G-sulfonic acid containing an excess of sodium bicarbonate. When developing is finished, the dyestuff is isolated and dried. It forms a redbrown water-soluble powder corresponding to the formula:

and dyeing the animal fiber bright equal red shades. When using as diam-component 4-am1no-d phenyl-ether or 2 amino 4' methyl-diphenylether or 2-amino-4-chlorordiphenyl-ether,"dyestufis of similar properties are obtained.

By replacing; the diazo-cornponent by the equivalent amount of. 4-amino-diphenyl-ether-2-sulionic acid ared' dyestuff is obtained dyeing wool equal shades of a very good fastness to light, fulling and perspiration; 7 z r11 In the same manner e.. g. 2:-benzoyl-aminoi-8- naphthol'-6- -sulfoni'c: acid on-th'e: urethane: of; the 2#amino-8-naphthoF6-sulfdnic acid may be used as combiningcomponents. it

y Examplev H By using in Example 1, paragraph 3; instead of 2-acetyl-amino-8 -naphthol -6-sulfonic: acid the same quantity of 2-acetyl-amino'-5'-naphtho1;-I;- sulfonic acid, a brick -red water-soluble dyestufi is obtained. which corresponds to the following formula:

and dyes wool from an acid bath bright orange shades of a very good fastness to light.

Still more yellowish dyestuffs of a similar brightness may be obtained by using as diazocomponents 4-amino-diphenyl-ether, 4-aminodiphenyl-ether 2 sulfonic acid, 4 amino di phenyl-ether-B-sulfonic acid, 2 -amino-diphenylether-4-sulfonic acid and so on.

A dyestuff of similar properties is formed by developing diazotized 4-amino-diphenyl-ether-2- sulfonic acid with 2-(2, 5'-dichloro-benzoyl)- methyl-amino-5-naphthol-7-sulfonic acid.

Example 3 18.5 parts of 4-amino-diphenyl-ether are diazotized in the usual manner. The diazo-solution is then allowed to run into a solution of 30 parts of Z-(acetyl methyl amino) -8-naphtho1-6-sulfonic acid containing the necessary amount of sodium bicarbonate. When developing is finished the dyestuff is isolated. It forms a red water-soluble powder which corresponds to the following formula:

SaH

dyeing wool very equal bright red shades which are fast to light.

By using as combiningcomponents 2- (benz oyl methyl-amino) --8-naphtho1-6-sulfonic acid 1 or 2- (acetyl-phenyl amino) 8 naphthol-G-sulfonic.

acid or 2- (acetyl-cyclohexyl-amino) -8-naphthol-" 6-sulfonic acid similar dyestuffs are obtainable.

Example 4 18.5 parts of 4-amino-diphenyl-ether are,di' V azotized as described in Example 1 and developed with a solution of 29 parts oil-acetyl-amino- 5-naphthol-7-sulfonic acid inthepresence of sodium bicarbonate. The dyestuif .thus obtained represents after isolating and'drying a brownred water-soluble powder and corresponds to the 7 following formula:

'It dyes theanimal fiber equalbright red shades.

' Verygood leveling bright red dyestuffs of very good fastness qualities are. obtained by developing the diazo-compoundof 2-amino-4-chloro-diphenyl-ether 'or of 4-amino-diphenyl-ether-2 wherein Y means a member of the group consisting of hydrogen, alkyl and phenyl, R means a member of the group consisting -ofzapetyl and benzoyl and wherein the phenyl nuclei contain a member of the group consisting of hydrogen,

halogen, and sulfonic acid, which dyestuffs dye animalfibers orange to red shades of agood leveling power and f astness' to light.

2. The monoazodyestufi of the formula:

NHOOCH:

which dyestufi forms a brick-red water-soluble powder and dyes'wool from an acid. bath bright orange shades of a very good fastness to light. v

3. The monoazodyestufi ofthe formula:

I 7 CH:

I COCH:

SOIH

which dyestufi forms a red powder and dyes wool very equal bright red shades fast to light. 4. The mono-azodyestufi of the formulaf which dyestuffs forms a brown-red powder and dyes the animal fiber equal bright red shades.

RICHARD FLEISCHHAUER. 

